CN1272843A - 4－氨基哌啶的纯化方法 - Google Patents
4－氨基哌啶的纯化方法 Download PDFInfo
- Publication number
- CN1272843A CN1272843A CN98809761A CN98809761A CN1272843A CN 1272843 A CN1272843 A CN 1272843A CN 98809761 A CN98809761 A CN 98809761A CN 98809761 A CN98809761 A CN 98809761A CN 1272843 A CN1272843 A CN 1272843A
- Authority
- CN
- China
- Prior art keywords
- amino
- piperadine
- described method
- purifying
- amino piperidine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- BCIIMDOZSUCSEN-UHFFFAOYSA-N piperidin-4-amine Chemical class NC1CCNCC1 BCIIMDOZSUCSEN-UHFFFAOYSA-N 0.000 title claims abstract description 36
- 238000000034 method Methods 0.000 title claims abstract description 30
- 239000003054 catalyst Substances 0.000 claims abstract description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
- 239000001257 hydrogen Substances 0.000 claims abstract description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000004821 distillation Methods 0.000 claims abstract description 8
- 239000011541 reaction mixture Substances 0.000 claims abstract description 5
- 238000005984 hydrogenation reaction Methods 0.000 claims description 17
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 11
- 239000010949 copper Substances 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 5
- 229910017052 cobalt Inorganic materials 0.000 claims description 5
- 239000010941 cobalt Substances 0.000 claims description 5
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 5
- 229910052802 copper Inorganic materials 0.000 claims description 5
- 229910052759 nickel Inorganic materials 0.000 claims description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 4
- MCMNRKCIXSYSNV-UHFFFAOYSA-N ZrO2 Inorganic materials O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 3
- 238000006356 dehydrogenation reaction Methods 0.000 claims description 3
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 3
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 claims description 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 2
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 229910052804 chromium Inorganic materials 0.000 claims description 2
- 239000011651 chromium Substances 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052737 gold Inorganic materials 0.000 claims description 2
- 239000010931 gold Substances 0.000 claims description 2
- 229910052741 iridium Inorganic materials 0.000 claims description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 229910052750 molybdenum Inorganic materials 0.000 claims description 2
- 239000011733 molybdenum Substances 0.000 claims description 2
- 229910052762 osmium Inorganic materials 0.000 claims description 2
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- 229910052702 rhenium Inorganic materials 0.000 claims description 2
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims description 2
- 229910052703 rhodium Inorganic materials 0.000 claims description 2
- 239000010948 rhodium Substances 0.000 claims description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 2
- 229910052707 ruthenium Inorganic materials 0.000 claims description 2
- 229910052709 silver Inorganic materials 0.000 claims description 2
- 239000004332 silver Substances 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- VRJHQPZVIGNGMX-UHFFFAOYSA-N 4-piperidinone Chemical class O=C1CCNCC1 VRJHQPZVIGNGMX-UHFFFAOYSA-N 0.000 abstract description 2
- -1 2,2,6,6-tetrasubstituted 4-amino-piperidines Chemical class 0.000 abstract 2
- 230000000887 hydrating effect Effects 0.000 abstract 1
- 239000000047 product Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 241001550224 Apha Species 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000005562 fading Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 150000003053 piperidines Chemical class 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000005576 amination reaction Methods 0.000 description 3
- 150000001414 amino alcohols Chemical class 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000005194 fractionation Methods 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- FTVFPPFZRRKJIH-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidin-4-amine Chemical class CC1(C)CC(N)CC(C)(C)N1 FTVFPPFZRRKJIH-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- JWUXJYZVKZKLTJ-UHFFFAOYSA-N Triacetonamine Chemical compound CC1(C)CC(=O)CC(C)(C)N1 JWUXJYZVKZKLTJ-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 238000004042 decolorization Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 1
- VDVUCLWJZJHFAV-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidin-4-ol Chemical compound CC1(C)CC(O)CC(C)(C)N1 VDVUCLWJZJHFAV-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229910000765 intermetallic Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- BDDWSAASCFBVBK-UHFFFAOYSA-N rhodium;triphenylphosphane Chemical compound [Rh].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 BDDWSAASCFBVBK-UHFFFAOYSA-N 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229960001866 silicon dioxide Drugs 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 238000001149 thermolysis Methods 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 230000003313 weakening effect Effects 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19743433A DE19743433C1 (de) | 1997-10-01 | 1997-10-01 | Verfahren zur Reinigung von 4-Amino-piperidinen |
| DE19743433.9 | 1997-10-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1272843A true CN1272843A (zh) | 2000-11-08 |
Family
ID=7844311
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN98809761A Pending CN1272843A (zh) | 1997-10-01 | 1998-09-25 | 4－氨基哌啶的纯化方法 |
Country Status (16)
| Country | Link |
|---|---|
| EP (1) | EP1025084A1 (de) |
| JP (1) | JP2001518465A (de) |
| KR (1) | KR20010030840A (de) |
| CN (1) | CN1272843A (de) |
| AU (1) | AU9746998A (de) |
| BR (1) | BR9812595A (de) |
| CA (1) | CA2305282A1 (de) |
| CO (1) | CO4770994A1 (de) |
| DE (1) | DE19743433C1 (de) |
| HU (1) | HUP0004584A2 (de) |
| ID (1) | ID23897A (de) |
| NZ (1) | NZ503565A (de) |
| PL (1) | PL339578A1 (de) |
| SK (1) | SK4262000A3 (de) |
| TW (1) | TW377345B (de) |
| WO (1) | WO1999016749A1 (de) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102008040045A1 (de) | 2008-02-01 | 2009-08-06 | Evonik Degussa Gmbh | Verfahren zur Herstellung von 4-Amino-2,2,6,6-tetramethylpiperidin |
| EP2085384A1 (de) | 2008-02-01 | 2009-08-05 | Evonik Degussa GmbH | Verfahren zur Herstellung von 4-Amino-2,2,6,6-tetramethylpiperidin |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3003843A1 (de) * | 1980-02-02 | 1981-08-13 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur herstellung von 4-amino-2,2,6,6-tetramethylpiperidin |
| CH664361A5 (de) * | 1985-06-13 | 1988-02-29 | Ni Institutkhimikatov Dlya Pol | Verfahren zur herstellung von 4-amino-2,2,6,6-tetramethylpiperidin. |
| US4766247A (en) * | 1986-09-26 | 1988-08-23 | Air Products And Chemicals, Inc. | Color reduction of polyamines by mild catalytic hydrogenation |
| JP2718179B2 (ja) * | 1989-05-26 | 1998-02-25 | 三井化学株式会社 | ２，２，６，６‐テトラアルキル‐４‐ピペリジノンの精製方法 |
| DE19622269A1 (de) * | 1996-06-03 | 1997-12-04 | Basf Ag | Verfahren zur Reinigung von sterisch gehinderten 4-Aminopiperidinen |
-
1997
- 1997-10-01 DE DE19743433A patent/DE19743433C1/de not_active Expired - Lifetime
-
1998
- 1998-09-25 NZ NZ503565A patent/NZ503565A/en unknown
- 1998-09-25 KR KR1020007003498A patent/KR20010030840A/ko not_active Application Discontinuation
- 1998-09-25 HU HU0004584A patent/HUP0004584A2/hu unknown
- 1998-09-25 SK SK426-2000A patent/SK4262000A3/sk unknown
- 1998-09-25 PL PL98339578A patent/PL339578A1/xx unknown
- 1998-09-25 WO PCT/EP1998/006117 patent/WO1999016749A1/de not_active Application Discontinuation
- 1998-09-25 JP JP2000513835A patent/JP2001518465A/ja not_active Withdrawn
- 1998-09-25 CA CA002305282A patent/CA2305282A1/en not_active Abandoned
- 1998-09-25 CN CN98809761A patent/CN1272843A/zh active Pending
- 1998-09-25 AU AU97469/98A patent/AU9746998A/en not_active Abandoned
- 1998-09-25 ID IDW20000612D patent/ID23897A/id unknown
- 1998-09-25 EP EP98951469A patent/EP1025084A1/de not_active Withdrawn
- 1998-09-25 BR BR9812595-8A patent/BR9812595A/pt not_active Application Discontinuation
- 1998-09-30 CO CO98056932A patent/CO4770994A1/es unknown
- 1998-09-30 TW TW087116216A patent/TW377345B/zh active
Also Published As
| Publication number | Publication date |
|---|---|
| EP1025084A1 (de) | 2000-08-09 |
| BR9812595A (pt) | 2000-08-01 |
| AU9746998A (en) | 1999-04-23 |
| CO4770994A1 (es) | 1999-04-30 |
| ID23897A (id) | 2000-05-25 |
| JP2001518465A (ja) | 2001-10-16 |
| HUP0004584A2 (hu) | 2001-04-28 |
| SK4262000A3 (en) | 2000-10-09 |
| TW377345B (en) | 1999-12-21 |
| CA2305282A1 (en) | 1999-04-08 |
| KR20010030840A (ko) | 2001-04-16 |
| NZ503565A (en) | 2001-09-28 |
| PL339578A1 (en) | 2000-12-18 |
| WO1999016749A1 (de) | 1999-04-08 |
| DE19743433C1 (de) | 1999-04-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2342177C (en) | Improved method for simultaneous preparation of 6-aminocapronitrile and hexamethylene diamine | |
| CN1068875C (zh) | 制备ε-己内酰胺和ε-己内酰胺前体的方法 | |
| CN1671646A (zh) | 仲胺的制备 | |
| KR100382618B1 (ko) | 3개이상의시아노기를갖는화합물로부터의아민의제조 | |
| EP0857719B2 (de) | Kontinuierliches Verfahren zur Herstellung von 4-Aminopiperidinen | |
| CN1121381C (zh) | 制备酮亚胺的新方法 | |
| CN1272843A (zh) | 4－氨基哌啶的纯化方法 | |
| KR101658666B1 (ko) | 4-아미노-2,2,6,6-테트라메틸피페리딘의 제조 방법 | |
| KR20030078038A (ko) | 디아민의 제조 방법 | |
| JPH05246926A (ja) | グリオキサール−又はアルキルグリオキサール−アセタールの製造方法 | |
| US5239120A (en) | Preparation of 2-(3-aminopropyl)-cycloalkylamines | |
| KR970011789B1 (ko) | 비스(2,2,6,6-테트라메틸-4-피페리딜)아민의 제조방법 | |
| CN1252054A (zh) | 连续制备ε－己内酰胺与其前体的含水混合物的方法 | |
| CA2337858A1 (en) | Improved method for simultaneous production of 6-aminocapronitrile and hexamethylenediamine | |
| CN1496356A (zh) | 制备n-取代的2,6-二烷基吗啉的方法 | |
| KR20230154915A (ko) | N,n'-비스(2,2,6,6-테트라메틸피페리딘-4-일)헥산-1,6-디아민을 제조하는 방법 | |
| CN1315941A (zh) | 连续制备ε－己内酰胺与ε－己内酰胺前体的含水混合物的方法 | |
| MXPA00002989A (en) | Method for purifying 4-amino-piperidines | |
| CN1088697C (zh) | 二聚体含量低的空间位阻4－氨基哌啶及其制备方法和应用 | |
| CZ20001042A3 (cs) | Způsob čištění 4-amino-piperidinů | |
| CN101263117A (zh) | 制备1-苄基-4-[(5,6-二甲氧基-1-二氢茚酮)-2-基]甲基哌啶或其盐酸盐的方法 | |
| EP2085385A1 (de) | Verfahren zur Herstellung von 4-Amino-2,2,6,6-tetramethylpiperidin | |
| JP2002001118A (ja) | 活性化された白金触媒及びそれを用いたアミンの製造法 | |
| JPH04187685A (ja) | 光学活性ナフチルエタノール誘導体の製造方法 | |
| CN1304405A (zh) | 丁内酯的制备 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
| WD01 | Invention patent application deemed withdrawn after publication |